Water → HCID 59749511, compound

HRID 747225Notes

Reaction equation

HRID 747225 reaction equation
[Si]([O:8][CH2:9][CH:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH2:31][C@H:30]([CH2:32][NH:33][C:34](=[O:36])[CH3:35])[O:29][C:28]4=[O:37])=[CH:23][C:22]=3[F:38])=[C:17]([F:39])[CH:16]=2)[CH2:11]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.O>ClCCl>[F:38][C:22]1[CH:23]=[C:24]([N:27]2[CH2:31][C@H:30]([CH2:32][NH:33][C:34](=[O:36])[CH3:35])[O:29][C:28]2=[O:37])[CH:25]=[CH:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH2:11][CH:10]([CH2:9][OH:8])[O:14][N:13]=2)=[CH:16][C:17]=1[F:39]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 59749449HCID 59749449, compound

Product 1

HCID 59749511HCID 59749511, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[((5S)-3-{4′-[5-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazol-3-yl]-2,2′-difluoro-1,1′-biphenyl-4-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide (416 mg, 0.74 mmol) was dissolved in dichloromethane (25 ml) at room temperature. A 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.82 ml, 0.82 mmol) was added and the reaction mixture stirred for 300 minutes. Water (50 ml) was added and the dichloromethane layer separated, dried over magnesium sulfate, filtered then concentrated in vacuo onto silica (2 ml). This was purified by chromatography (20 g silica gel bond elut; 0 to 6% methanol/dichloromethane) to yield 125 mg (38%) of the desired compound.

Workup

  1. customthe dichloromethane layer separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthen concentrated in vacuo onto silica (2 ml)
  5. customThis was purified by chromatography (20 g silica gel bond elut; 0 to 6% methanol/dichloromethane)

Sources & evidence

ORD record
ord-c72ea29bd4ab461bbd8dd9437af86d51
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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